Reaktion #48043

Reaktionsgleichung

1-(4-bromophenyl)-cyclobutanol

triethylsilane

→

1-bromo-4-cyclobutyl-benzene

Ausbeute 66.3%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThen 1.15 ml of boron trifluoride diethyl etherate complex were added
2. 2
   Temperaturthe reaction mixture was warmed to −40° C.
3. 3
   SonstigeThe reaction was then quenched by addition of 10% aqueous KHCO3
4. 4
   Extraktionthe mixture was extracted three times with DCM
5. 5
   WaschenThe combined extracts were washed with brine
6. 6
   Trocknendried with magnesium sulfate
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe remaining residue was purified by column chromatography (silica gel; cyclohexane)

Vorschrift

To a solution of 1.37 g of 1-(4-bromophenyl)-cyclobutanol (6 mmol) in 15 ml DCM were added 1.15 ml of triethylsilane (7.2 mmol) and the mixture was cooled to −78° C. Then 1.15 ml of boron trifluoride diethyl etherate complex were added and the reaction mixture was warmed to −40° C. and stirred for 8 h. The reaction was then quenched by addition of 10% aqueous KHCO3 and the mixture was extracted three times with DCM. The combined extracts were washed with brine, dried with magnesium sulfate and concentrated. The remaining residue was purified by column chromatography (silica gel; cyclohexane) to give 0.84 g (66%) of 1-bromo-4-cyclobutyl-benzene as a colorless liquid. 1H NMR (CDCl3, 300 MHz): δ 1.85 (m, 1H), 1.92-2.18 (m, 3H), 2.33 (m, 2H), 3.49 (quint, J=8.5 Hz, 1H), 7.08 (d, J=8.5 Hz, 2H), 7.40 (d, J=8.5 Hz, 2H).

Quelle